Cesium carbonate → 1-(2,5-Difluorophenyl)cyclohex-1-ene

HRID 1817837Notes

Reaction equation

FC(F)(F)S([C:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].[F:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1B(O)O>C(COC)OC.O>[F:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[C:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1-Trifluoromethylsulphonylcyclohex-1-ene (3 g, 13 mmol), cesium carbonate (8.4 g, 26 mmol) and 2,5-difluorophenyl boronic acid (2.88 g, 18 mmol) were dissolved in dimethoxyethane/water [9:1] (200 ml). The flask was degassed and then tetrakistriphenylphosphine palladium (125 mg) was added, the mixture warmed to 80° C. over 4 hr and then cooled to r.t. The solution was filtered through Celite™, diluted with water (20 ml) and the solution washed with ethyl acetate (2×100 ml). The organic phase washed with brine (100 ml), dried (MgSO4) and evaporated. The clear oil obtained was purified by column chromatography on silica gel eluting with hexanes, to give 1-(2,5-difluorophenyl)cyclohex-1-ene. 1H NMR (CDCl3) 6.97-6.73 (3H, m), 5.97-5.96 (1H, m), 2.35-2.31 (2H, m), 2.23-2.14 (2H, m) and 1.79-1.68 (1H, m).

Workup

customThe flask was degassed
additiontetrakistriphenylphosphine palladium (125 mg) was added
temperaturecooled to r.t
filtrationThe solution was filtered through Celite™
additiondiluted with water (20 ml)
washthe solution washed with ethyl acetate (2×100 ml)
washThe organic phase washed with brine (100 ml)
dry with materialdried (MgSO4)
customevaporated
customThe clear oil obtained
customwas purified by column chromatography on silica gel eluting with hexanes

Sources & evidence

ORD record: ord-a83deddccef449b1a3088e032c742803
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598386B2

Reaction notes

Loading…